A New Reaction of 2-(Phenylsulfonyl)-3-phenyloxaziridine (Davis Reagent): Oxidation of Thiolates to Sulfinates. Application to the Synthesis of Sulfones

F Sandrinelli, S Perrio, P Beslin

Index: Sandrinelli, Franck; Perrio, Stephane; Beslin, Pierre Organic Letters, 1999 , vol. 1, # 8 p. 1177 - 1180

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Citation Number: 25

Abstract

The first efficient and general method for the generation of sulfinate anions by oxidation of the corresponding thiolates is described. The oxidizing agent employed is the classical 2- (phenylsulfonyl)-3-phenyloxaziridine, commonly known as the Davis reagent. Subsequent S- alkylation of the sulfinates under phase-transfer catalysis affords sulfones 6 in 71-91% isolated yields (10 examples).